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Jay Cutler is rolling in the dough after signing a multi-million dollar extension, but you'd never guess that by his choice of wheels at training camp. (Published Wednesday, Jul 23, 2014)

For Chicago Bears quarterback Jay Cutler, the 2014 season isn’t just about winning a championship or beginning to earn the seven-year contract that he signed in January, but instead, it’s about establishing what his legacy is going to be as an NFL player.

That’s because all of the pieces are finally in place for him to become a success in the league. He has the long-term guaranteed money-laden contract that gives him the security that all football players crave. He has weapons like Brandon Marshall, Alshon Jeffery, and Martellus Bennett that are there for him to use to gut opposing defenses. Most importantly of all however, he has a coach that has a reputation as a “quarterback whisperer,” and has turned quarterbacks far less talented than Cutler into All-Pro caliber players.

Cutler Shows Up to Camp in Conversion Van

Jay Cutler is rolling in the dough after signing a multi-million dollar extension, but you'd never guess that by his choice of wheels at training camp. (Published Wednesday, Jul 23, 2014)

Even with all of these advantages, there is still some question as to whether or not Cutler will be able to make the most of the situation he finds himself in. He still has a reputation, deserved or not, as a hard nut to crack, going through offensive coordinators with such speed that some believe he is impossible to work with. That unwillingness to curtail his style of play has hindered his standing in the eyes of NFL observers and fans, but while Cutler may not care about these types of things, it may also prove to be a stumbling block as he tries to become the franchise quarterback that the Bears’ brass has always envisioned him to be.

In his first year under Trestman’s tutelage, Cutler did make some significant progress in those areas, but also had occasional relapses. He threw for 2621 yards and 19 touchdowns, but he still threw 12 interceptions on the season, and the team missed the playoffs for the fourth time in his five seasons in the Windy City.

Cutler Talks About Bears Time Away From His Kids

Jay Cutler talked to the media ahead of his charity beach volleyball tournament at North Avenue Beach. Cutler said he's looking forward to camp and the upcoming season, but not about being away from his kids. (Published Friday, Jul 18, 2014)

Complicating matters again for Cutler was the fact that he couldn’t get through the season without succumbing to injury, something that has happened in four consecutive seasons. In total, he missed five games with injuries, and even though Josh McCown proved to be a capable back-up, it’s still entirely possible that the missed time ended up hindering Cutler’s performance at the end of the season.

This year, Cutler’s health will be even more crucial, as the team will potentially have an inexperienced man at the controls in his absence. Jordan Palmer has been given the first shot at backing Cutler up this season, and he has attempted a grand total of 15 passes in his six year NFL career. He hasn’t thrown a single touchdown, but has completed 10 of those passes.

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Jimmy Clausen could end up winning the role too, but regardless of who ends up holding the clipboard on the Bears’ sideline, the fact remains that Cutler is the key to everything. If he goes down, the season pretty much goes up in smoke, and no amount of Trestman magic would likely be enough to save it.

With an arsenal of weapons at his disposal and a coach ready to tailor a system to his skillset, Cutler has everything he needs to succeed, and he’s out of excuses for not doing so. It’s make or break time for the Bears’ quarterback, and his fortunes will mirror those of the team he is trying to lead back to the promised land.